1.14.14.99: (S)-limonene 3-monooxygenase
This is an abbreviated version!
For detailed information about (S)-limonene 3-monooxygenase, go to the full flat file.
Word Map on EC 1.14.14.99
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1.14.14.99
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mentha
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peppermint
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monoterpene
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regiospecific
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limonene-6-hydroxylase
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piperita
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spearmint
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flavor
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monoterpenoids
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citrus
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4s-limonene
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olefin
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fragrance
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agriculture
- 1.14.14.99
-
mentha
- peppermint
-
monoterpene
-
regiospecific
- limonene-6-hydroxylase
- piperita
- spearmint
-
flavor
-
monoterpenoids
-
citrus
-
4s-limonene
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olefin
-
fragrance
- agriculture
Reaction
Synonyms
(-)-limonene 3-hydroxylase, (-)-limonene 3-monooxygenase, (-)-limonene,NADPH:oxygen oxidoreductase (3-hydroxylating), (-)-limonene-3-hydroxylase, EC 1.14.13.47, L3oh, limonene-3-hydroxylase, More, oxygenase, (-)-limonene 3-mono-, PM17
ECTree
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Substrates Products
Substrates Products on EC 1.14.14.99 - (S)-limonene 3-monooxygenase
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REACTION DIAGRAM
(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
(-)-(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
(-)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone
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(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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53% the rate of (-)-limonene hydroxylation
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?
(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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hydroxylation at 50%
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?
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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?
(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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i.e. (+)-8,9-dihydro-limonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
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(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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limonene 6-hydroxylase mutant F363I
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(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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highly specific, regiospecific and stereospecific reaction
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?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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highly specific, regiospecific and stereospecific reaction
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?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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highly specific, regiospecific and stereospecific reaction
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?
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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(-)-(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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the enzyme is involved in biosynthesis of peppermint essential oil monoterpenes
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(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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?
(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
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i.e. (-)-8,9-dihydrolimonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
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?
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
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no substrates: isolimonenes, terpinolene, alpha- or beta-phellandrene, alpha- or beta-terpinene, bicyclic monoterpenes: pinene, sabinene, alpha-thujene, p-cymene, cis- or trans-p-menthane, highly specific, absolute requirement for a reduced pyridine nucleotide and molecular oxygen
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additional information
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the kinetically competent recombinant protein produces a mixture of C3-, C6- and C7-hydroxylated limonene derivatives, i.e. (-)-perillyl alcohol, (-)-trans-isopiperitenol, and (-)-trans-carveol, with a distribution of 33%, 14% and 53%, respectively, thus it performs the reaction of EC 1.14.13.47 and 1.14.13.48, overview
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